This invention relates to hydroxymethylbenzenesulfonamide derivatives which are useful as agricultural chemicals and in particular as general herbicides having both pre- and post-emergence activity.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl. PA1 R is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; PA1 R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.2 is H or CH.sub.3 ; PA1 R.sub.8 is H, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.11 is H, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkynyl, C.sub.3 -C.sub.4 cycloalkyl, ##STR9## C.sub.1 -C.sub.4 alkyl substituted with 1-4 substituents selected from 0-3 F., 0-3 Cl or 0-3 Br, or C.sub.2 -C.sub.3 alkenyl substituted with 1-3 Cl; PA1 R.sub.12 is H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.5 -C.sub.6 cycloalkyl, ##STR10## C.sub.5 -C.sub.6 cycloalkyl substituted with CH.sub.3 ; R.sub.13 is C.sub.1 -C.sub.6 alkyl or ##STR11## R.sub.14 and R.sub.15 are independently H, NO.sub.2, CH.sub.3, Cl or OCH.sub.3 ; PA1 R.sub.16 is H, F, Cl, Br, C.sub.1 -C.sub.3 alkyl, NO.sub.2, CN, SO.sub.2 CH.sub.3, OCH.sub.3, SCH.sub.3 or CF.sub.3 ; PA1 R.sub.17 H, Cl or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.18 is H, CH.sub.3 or Cl; PA1 A is ##STR12## W is O or S; X is H, Cl, Br, CH.sub.3, CH.sub.2 CH.sub.3, C.sub.1 -C.sub.3 alkoxy, CF.sub.3, SCH.sub.3 or CH.sub.2 OCH.sub.3 ; PA1 Y is CH.sub.3 or OCH.sub.3 ; PA1 Z is N, CH, CCl, CBr, CCN, CCH.sub.3, CCH.sub.2 CH.sub.3, CCH.sub.2 CH.sub.2 Cl or CCH.sub.2 CH.dbd.CH.sub.2 ; PA1 Y.sup.1 is H, CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; and PA1 Q is O or CH.sub.2 ; PA1 (a) The compound of Formula XV can be suspended or dissolved in an alkanol solvent in the presence of at least two equivalents of alkoxide. The alkoxide can be added directly as alkali metal or alkaline earth metal alkoxide or can be generated by the addition to the alkanol solvent of at least two equivalents of a base capable of generating alkoxide from the solvent. Suitable bases include, but are not limited to, the alkali and alkaline earth metals, their hydrides and tert-butoxides. For example, when X is methoxy, the compound of Formula XV could be suspended or dissolved in methanol in the presence of two equivalents of sodium methoxide. Alternatively, two equivalents of sodium hydride could be used in place of the sodium methoxide. PA1 (b) The compound of Formula XV can be suspended or dissolved in an inert solvent in the presence of at least two equivalents of alkoxide. Suitable inert solvents include, but are not limited to, acetonitrile, THF and dimethylformamide. The alkoxide may be added directly as alkali metal or alkaline earth metal alkoxide or may be generated from alkanol and a base as described in (a) above. For example, when X is methoxy, the compound of Formula XV could be suspended or dissolved in THF in the presence of two equivalents of sodium methoxide. Alternatively, two equivalents each of methanol and sodium hydride could be used instead of sodium methoxide.
U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2## wherein R.sub.1 is hydrogen or lower saturated aliphatic acyl and
The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides as being useful as antidiabetic agents: ##STR3## wherein R.dbd.H, halogen, CF.sub.3 or alkyl.
Logemann et al. Chem Ab., 53, 18052 g (1969), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR4## wherein R is butyl, phenyl, or ##STR5## and R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR6## Based upon similarity to a known compound, the author speculated that the foregoing compound might have a hypoglycemic activity.
Substituted-pyrimidinyl sulfonylureas of the following formula, which are also para-substituted on the phenyl ring, are disclosed in Farmco Ed. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959]: ##STR7## wherein R.dbd.H or CH.sub.3.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.